Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/039—Disazo dyes characterised by the tetrazo component
  • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
  • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
  • C09B35/18—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/039—Disazo dyes characterised by the tetrazo component
  • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/039—Disazo dyes characterised by the tetrazo component
  • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
  • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
  • C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B41/00—Special methods of performing the coupling reaction
  • C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium

Definitions

• the present invention is concerned with valuable new disazo dyestuffs, and a process for preparing the same.
• the present invention is particularly concerned with direct dyeing cotton dyestuffs (also called substantive dyestuffs), and still more particularly with dyestuffs capable of being metallized, for instance coppered, in substance, in the dyebath or on the fiber, as the case may be.
• tetrazotized 3 3'-dihydroXy-4 4'-diaminodiphenyl is coupled with two molecular proportions of coupling components as defined hereinafter.
• 3 3'-dihydroxy-4 4-diaminodiphenyl which is a known compound and which may be obtained for instance by saponifying dianisidine by means of aluminum chloride, has not hitherto found any industrial use.
• a few dyestuffs prepared with tetrazotized 3:3'-dihydroxy-ben zidine have been described in the literature, the said compound has generally been regarded to be of no practical value. This is probably due to several facts. First of all it was generally believed that the said product would be too expensive for the commercial manufacture of dyestuffs.
• coupling may be carried out with two molecular proportions of 2 the same coupling component.
• it is not unduly difiicult to effect coupling with two different coupling components since tetrazotized 3:3-dihydroxy-4:4'-diaminodiphenyl has a great tendency to couple first with one diazo group and afterwards with the other.
• 3 3'-dihydroxy-4 4' -diaminodiphenyl may be obtained by saponification of dianisidine by means of aluminum chloride and may be purified if necessary according to known methods. It may be tetrazotized in known manner and the tetrazo compound may be used immediately after tetrazotizing or may be separated, as described in the examples below.
• a tetrazotised 3:3 -dihydroxy-4:4'-diaminodiphenyl is united with 2 molecular proportions of the same or difierent coupling components of which at least one is a hydroxynaphthalene free from sulfonic acid groups.
• Such hydroxynaphthalenes are used according to this feature of the invention which contain neither a sulfonic acid group as nuclear substituent nor in external linkage. It is advantageous that these hydroxynaphthalenes should be completely free from any substituents which have a strong solubilizing action such as carboxylic acid groups. They may advantageously contain at least one further substituent, preferably only one further substituent of another kind, for example an auXo-chromic group, such as a hydroxyl group, an amino (including substituted amino) group, an alkoxy group or a sulphamido group, and these substituents may, for example, be distributed on the two benzene rings forming the naphthalene nucleus. It will be advantageous to use such hydroxynaphthalenes which permit a coupling in the ortho-position to the hydroxyl group.
• Such components are, for example, the various dihydroxynaphthalenes, such as -1:5-, 2:6- and -2:7-dihydroxynaphthalene, 2-amino-7-hydroxynaphthalene, 1-amino-7-hydroxynaphthalene, 2:6-dihydroxynaphthalene monoglycerine ether, as well as N-substituted amino-hydroxynaphthalenes, in which the amino group, for example, can be substituted by alkyl or hydroxyalkyl radicals.
• hydroxynaphthalenes also come into consideration which con- 3 tain other substituents besides those mentioned above, e. g., a sulfonamide group.
• hydroxynaphthalenes which are absolutely free from water solubilizing groups and, for example, are also free from carboxyl groups.
• These dyestuffs can be advantageously dyed from baths rendered alkaline with alkali hydroxide.
• a tetrazotized 3:3-dihydroxy-4:4'-diaminodiphenyl is coupled with two molecular proportions of coupling components at least one of which is a l-hydroxynaphthalene containing an auxochromic group in the 8-position.
• auxochromic groups are, for instance, an amino or a substituted amino group, or a further hydroxyl group, or any other group possessing auxo chrome properties.
• These coupling components may carry further substituents in suitable positions of the naphthalene nucleus, for instance nonsolubilizing substituents, such as halogen.
• coupling is effected in an alkaline medium. It is to be remarked, however, that there are many coupling components, especially those of the naphthalene series, which do not combine in a satisfactory manner with tetrazotized 3:3-dihydroxy-4:l'- diaminodiphenyl when coupling occurs in the usual manner, i. e., in a medium alkaline with sodium carbonate, even if pyridine or similar promoters are added. The combination is often incomplete to such an extent that only little or no disazo dyestuff is produced, and a monoazo dyestufif is obtained as main product.
• reaction media are properly used coinbination may also be effected with Z-hyd'roXynaphthalene sulfo'nic acids, such as Z-hydrox-ynaphthalene-fi-sulfonic acid, 2-hydroxynaphthalene-3z6-disulfonic acid, as well as with 2- amino 5 hydroxynaphthale'ne-7-sulfonic acid and 2 -amino-5-hydroxynaphthalene- 1 7-disulfonic acid, substantially avoiding the production of monoazo-dyestuffs.
• Z-hyd'roXynaphthalene sulfo'nic acids such as Z-hydrox-ynaphthalene-fi-sulfonic acid, 2-hydroxynaphthalene-3z6-disulfonic acid, as well as with 2- amino 5 hydroxynaphthale'ne-7-sulfonic acid and 2 -amino-5-hydroxynaphthalene- 1 7-
• the disazo dyestuffs of the present invention are suitable for dyeing and printing the most diverse, materials, especially cellulose fibers, such as cotton and other vegetable fibers, rayon from regenerated cellulose including staple fibers, and also for dyeing and printing animal fibers such as wool, 'silk and leather. Due to the fact that the said dyestuffs are derived from an ortho-hydroxydiazo compound they are capable of forming complex metal compounds, for instance, with the metals copper, cobalt, nickel, iron, chromium,
• Whether it is preferable to produce the aforementioned complex metal compounds on the fiher or in substance depends on various properties thereof, inter alia, whether the complex metal compounds are soluble, whether the metal-free dyestuffs possess sufiicient afiinity for the fiber to be dyed, etc.
• Example 1 21.6 parts of 3:3'-dihydroxy-4:4'-diaminodiphenyl, in the form of its dichlorhydrate, are
• Example 2 21.6 parts of 3':3'-dihydroxy-4:4-diaminodiphenyl are tetrazotized and the reaction mixture neutralized and the tetrazo compound filtered off.
• the dried powder is a black bronzy substance which yields navy blue shades with very good fastness properties on being dyed and coppered on cotton by either a one or two bath process.
• Example 5 21.6 parts of 3:3'-dihydroxy-4:4'-diarninodiphenyl are tetrazotized as in Example 4 and filtered off.
• Example 6 21.6 parts of 3:3'-dihydroxy-4:4'-diaminodiphenyl are tetrazotized and the neutralized tet- I razo compound filtered ofi'.
• the new dyestufi when dry is a violet-black powder insoluble in water. When dissolved in soda of 10 percent strength and in concentrated sulfuric acid, it yields a blue and when dissolved in caustic soda solution of 10 percent strength it yields a blackish red solution. It produces navy blue shades of very good fastness properties on being dyed and coppered on cotton by either a one or two bath process.
• Example 7 21.6 parts of 3:3'-dihydroxybenzidine are tetrazotized in known manner in the presence of hydrochloric acid with sodium nitrite.
• the crystalline precipitated tetrazo compound is added at 5 C. to a solution of 44.6 parts of l-naphthol-8-sulfonamide in 36 parts by volume of a caustic potash solution of 50 percent by weight KOH.
• the temperature increases spontaneously to 30 C.
• Coupling is carried out for two days at 25 to 30, then the coupling mixture is diluted with 800 parts of hot water and after boiling for a short period the dyestufi is salted out.
• the dyestufi is filtered ofi and after drying represents a dark green bronzy powder which dissolves in water and cold soda solution to a bordeaux red, in hot soda solution and caustic alkalies to a violet and in concentrated sulfuric acid to a greenish blue solution. It yields navy blue shades which are fast to washing and to light on being dyed and coppered on vegetable fibers by either a one or two bath process.
• Example 8 2.5 parts of the dyestufi obtained according to Example '7 are dissolved hot in 250 parts of water with the addition of a little caustic soda solution. This solution is added to a dye bath consisting of 2000 parts of water and 2 parts of sodium hydroxide. At 50 C. 100 parts of well we'tted cotton are entered and the temperature raised to 95 C. within half an hour, and then 30 parts of Glaubers salt are added. After dyeing for about A of an hour at this temperature the bath is allowed to cool to C., and then 2 parts of a complex copper sodium tartrate are added and coppering carried out for half an hour at from 80 to C. The cotton is well rinsed and if necessary soaped. It is dyed a fast navy blue.
• hydroxide of the alkali metal series includes aqueous solutions of ammonia.
• m consisting of hydroxyl, amino, azlkoxy andsulf- 9; The disazb dystufl of the formula amidegroup's. v c l 2.
• Disazo dyestuffs of the general formula; OON I -I 61; OH 03 wherein it; and R2 stand for redicais 6f difiy-
• Disazo dyestuffs of the general formula- I III- NN I' ⁇ I NR' N N QC? 1 AH 6H 7 $11 1': 11. The disazo djiestu'fi of the formula.
• Disalzo dyestuffs or the genera formula PETER PIETH 4. Disalzo dyestuffs or the genera formula PETER PIETH.
• R1 ana R2 stand for radicals of h'ydroxy I nafil'ithal'ene sulfami'd'e coupnn' component's free REFERENCES CITED from-furthe'r'substituentsi V I m
• R1 ana R2 stand for radicals of h'ydroxy I nafil'ithal'ene sulfami'd'e coupnn' component's free REFERENCES CITED from-furthe'r'substituentsi V I m

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